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CM1000 – Organic Chemistry An Introduction to Functional Group Chemistry

CM1000 – Organic Chemistry An Introduction to Functional Group Chemistry. Dr. Stuart Collins. Recommended text: Hart, Craine, Hart, Organic Chemistry 11 th Edition. Course Content. Chapter 6- Organic Halogen Compounds Chapter 7- Alcohols, Phenols and Thiols

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CM1000 – Organic Chemistry An Introduction to Functional Group Chemistry

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  1. CM1000 – Organic ChemistryAn Introduction to Functional Group Chemistry Dr. Stuart Collins Recommended text: Hart, Craine, Hart, Organic Chemistry 11th Edition

  2. Course Content • Chapter 6- Organic Halogen Compounds • Chapter 7- Alcohols, Phenols and Thiols • Chapter 9- Aldehydes and Ketones • Chapter 10- Carboxylic Acids and Their Derivatives • Chapter 11- Amines and Related Nitrogen Compounds

  3. Organic Chemistry Structure Reactivity • Characteristic Behaviour • Can be rationalised and • predicted Carbon Framework Functional Groups Significance? Design of structure Function Synthesis

  4. Organic Halogen Compounds • Why important? • CFC’s • Chlorofluorocarbons (p.196) • Environmental Impact • Insecticides (p.198) • Key Synthetic Intermediates Provide Access To A Wide Range Of Organic Compounds General Structure

  5. Classification- Depends on Degree of Substitution

  6. Reactivity Strongly Influenced by Degree of Substitution Nucleophilic Substitution Halide displaced by an incoming nucleophile- a species with an electron pair. Nucleophile can be neutral or anionic

  7. Recall X more electronegative than C – Bond is polarised One covalent bond broken (C-X) One new covalent bond (C-Nu)

  8. Neutral Nucleophiles

  9. Williamson Ether Synthesis

  10. Elimination Reactions- Dehydrohalogenation (6.7) Loss of halide (X-) from one carbon and loss of a proton (H+) from adjacent carbon- new alkene Usually occurs on treatment with a base e.g. Na+-OEt

  11. Bases Commonly used to Promote Elimination Reactions

  12. Mechanism

  13. Example Elimination can occur from either side of the alkyl bromide - 2 alkenes (Regioisomers)

  14. Cis and trans isomers can be formed in some cases Both cis and trans isomers can be formed in the internal elimination

  15. Elimination/Substitution- May be competing reactions

  16. By altering the reaction conditions can favour either • elimination or substitution • Vary solvent (Polar/Non-Polar) • Vary base or nucleophile • In general strong bases favour elimination • Nucleophiles which are weak bases favour substitution

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